30483-75-1

Basic information

• Product Name: N-(4-BROMOPHENYL)MORPHOLINE
• Synonyms: 4-(4'-BROMOPHENYL)MORPHOLINE;N-(4-BROMOPHENYL)MORPHOLINE;1-Bromo-4-morpholinobenzene;4-(4-Bromophenyl)morpholine 97%;Morpholine,4-(4-bromophenyl)-
• CAS NO: 30483-75-1
• Molecular Formula: C₁₀H₁₂BrNO
• Molecular Weight: 242.11
• Product Categories: pharmacetical;Miscellaneous;Building Blocks;Chemical Synthesis;Halogenated Heterocycles;Heterocyclic Building Blocks;Morpholines/Thiomorpholines
• Mol File: 30483-75-1.mol
• Article Data: 59

Chemical Properties

• Melting Point: 114-118 °C(lit.)
• Boiling Point: 341.198 °C at 760 mmHg
• Flash Point: 160.151 °C
• Appearance: /
• Density: 1.433 g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.574
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: 4.33±0.40(Predicted)
• CAS DataBase Reference: N-(4-BROMOPHENYL)MORPHOLINE(CAS DataBase Reference)
• NIST Chemistry Reference: N-(4-BROMOPHENYL)MORPHOLINE(30483-75-1)
• EPA Substance Registry System: N-(4-BROMOPHENYL)MORPHOLINE(30483-75-1)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• Hazardous Substances Data: 30483-75-1(Hazardous Substances Data)

Usage

Uses

N-(4-BROMOPHENYL)MORPHOLINE is used as organic synthesis intermediate and pharmaceutical intermediate, mainly used in laboratory research and development process and chemical production process.

Synthesis

In an open flask, 10 mL of 1.5 M NaBr in pH 6.2 phosphate buffer (0.23 M in PO4) or pH 4.2 phosphate buffer (5% NaH2PO4) was added to a solution of 1 mmol of substrate dissolved in 9.75 mL of distilled 1,4- dioxane. To this mixture was added a freshly made solution of diphenyl ditelluride (1e, 0.25 mL of a 10 mM stock in 1,4-dioxane, 2.5 μmol, 0.25 mol % relative to substrate) followed by the addition of 8.8 M H2O2 according to Table 3. The reaction mixture was stirred at room temperature for the appropriate amount of time and was then diluted with 10 mL of water. The resulting solution was extracted with EtOAc (3 × 10 mL), and the combined organic extracts were washed with 0.5 M NaHSO3 (5 mL) and brine (10 mL), dried over MgSO4, and concentrated. Yields reported below are the mean of duplicate runs. N-(4-Bromophenyl)morpholine (21):28 product isolated as a tan solid (224 ± 1 mg, 93% yield). Mp 111-113 °C (lit.28 mp 111-112 °C).

InChI:InChI=1/C10H12BrNO/c11-9-1-3-10(4-2-9)12-5-7-13-8-6-12/h1-4H,5-8H2

Upstream product

• 110-91-8 morpholine 
• 106-37-6 1.4-dibromobenzene 
• 66107-30-0 4-bromophenyl trifluoromethanesulfonate 
• 321970-34-7 1,1,2,2,3,3,4,4,4-nonafluorobutane-1-sulfonic acid 4-bromophenyl ester 
• 92-53-5 4-Phenylmorpholine 
• 5765-65-1 4-(benzoyloxy)morpholine 
• 183677-71-6 2-(4-bromophenyl)-5,5-dimethyl-1,3,2-dioxaborinane 
• 589-87-7 1,4-bromoiodobenzene 
• 108-86-1 bromobenzene 
• 186498-02-2 4-(4-morpholinyl)phenylboronic acid 
• 586-78-7 para-nitrophenyl bromide 
• 2524-67-6 4-morpholino-4-yl-phenylamine 
• 10389-51-2 1-morpholino-4-nitrobenzene 
• 742099-65-6 5-bromo-2-(morpholin-4-yl)benzaldehyde 

Downstream Products

• 693242-87-4 4-morpholino-1-[14C]-benzoic acid 
• 30483-78-4 2-(2-bromo-phenylsulfanyl)-5-morpholin-4-yl-aniline 
• 31618-92-5 N-[2-(2-bromo-phenylsulfanyl)-5-morpholin-4-yl-phenyl]-acetamide 
• 30483-77-3 4-[4-(2-bromo-phenylsulfanyl)-3-nitro-phenyl]-morpholine 
• 31618-93-6 N-[2-(2-bromo-phenylsulfanyl)-5-morpholin-4-yl-phenyl]-diacetamide 
• 216989-48-9 2-methyl-1-(4-morpholinophenyl)propan-1-one 
• 1070716-76-5 3-(1,3-benzodioxol-5-yl)-2-methyl-2-[4-(4-morpholinyl)phenyl]propanal 
• 1160526-70-4 5-methyl-5-(4-morpholinophenyl)furan-2-one 
• 10282-31-2 4-morpholinobenzonitrile 
• 23676-05-3 4-morpholin-4-yl-benzoic acid methyl ester 
• 162848-18-2 4-(morpholin-4-yl)benzoyl chloride 

Relevant articles and documents

The surprisingly facile formation of Pd(i)-phosphido complexes from: Ortho -biphenylphosphines and palladium acetate

The widely-used ortho-biphenylphosphine ligands SPhos and RuPhos not only undergo facile orthometallation with palladium acetate, yielding strained, four-membered dimeric palladacycles but more surprisingly, in the presence of alcoholic solvents, along with the less encumbered analogue MePhos, yield unusual dinuclear Pd(i) complexes, in which the Pd-centers are bridged by both a phosphide ligand and by the arene of a coordinated phosphine donor.

Amination of Aryl Halides Mediated by Electrogenerated Nickel from Sacrificial Anode

Electrochemical C(sp2)?N couplings mediated by nickel salts generated from the sacrificial anode has been described for the first time. In this approach, the sacrificial nickel anode is employed as the sole source of nickel and the process, operationally simple to set up, enables the preparation of functionalized arylamine derivatives with moderate to good yields, under mild reaction conditions and without additional ligand. A cooperative process between the two electrodes is involved in the proposed mechanism.

Direct bromodeboronation of arylboronic acids with CuBr2 in water

An efficient and practical method has been developed for the preparation of aryl bromides via the direct bromodeboronation of arylboronic acids with CuBr2 in water. This strategy provides several advantages, such as being ligand-free, base-free, high yielding, and functional group tolerant.